Results in Chemistry ( IF 2.5 ) Pub Date : 2020-10-22 , DOI: 10.1016/j.rechem.2020.100075 Axel Steinbrueck , James T. Brewster , Michael Y. Zhao , Adam C. Sedgwick , Jonathan L. Sessler
Herein, we describe a detailed preparation of the versatile pyrrole building block 3,4-diethylpyrrole-2-carboxylate (1), a key structural feature in various porphyrins, porphyrinoids, and other chromophores. 1 was prepared via a one-pot DBU catalyzed Henry reaction and acid catalyzed acetylation followed by an aqueous workup and telescoping through an adapted Magnus-Schöllkopf-Barton-Zard cyclization protocol from commercial starting materials. The three-step preparation utilized new chemistry, requires only one formal purification step, and affords 1 at 86% yield and >99% purity on a decagram scale.
中文翻译:
方便的十克规模的乙基3,4-二乙基吡咯-2-羧酸乙酯的制备,这是吡咯基大环和生色团的通用前体
在这里,我们描述了多功能吡咯结构单元3,4-二乙基吡咯-2-羧酸盐(1)的详细制备,这是各种卟啉,卟啉类和其他生色团的关键结构特征。1经一锅DBU催化Henry反应和酸催化的乙酰化,随后水后处理和伸缩通过适于从商业起始材料马格纳斯Schöllkopf-巴顿ZARD环化方案制备。该三步制备方法采用了新的化学方法,仅需一个正式的纯化步骤即可提供,以十克计,收率为86%,纯度> 99%,为1。